N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-diphenylmethylthiourea | 313695-72-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-diphenylmethylthiourea
• 英文别名: 1-[(1S,2S)-2-amino-1,2-diphenylethyl]-3-benzhydrylthiourea
• CAS: 313695-72-6
• 化学式: C₂₈H₂₇N₃S
• 分子量: 437.608
• InChiKey: CVNWEPPUTGMNGI-BDYUSTAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-diphenylmethylthiourea 在 2-氯-1,3-二甲基氯化咪唑啉 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (4S,5S)-1-benzoyl-4,5-diphenyl-2-(diphenylmethylimino)imidazolidine
  参考文献：
  名称：

  Modified Guanidines as Potential Chiral Superbases. 2. Preparation of 1,3-Unsubstituted and 1-Substituted 2-Iminoimidazolidine Derivatives and a Related Guanidine by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas

  摘要：

  Simple preparation methods for modified guanidines were explored for new chiral superbases, Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S)-1,2-diphenylethylenediamine and (1R,2R)- or (1S,2S)-1,2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,SS)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.

  DOI：

  10.1021/jo000745n
• 作为产物：
  描述：

  二苯甲胺 在 2-氯-1,3-二甲基氯化咪唑啉 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 146.0h， 生成 N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-diphenylmethylthiourea
  参考文献：
  名称：

  Modified Guanidines as Potential Chiral Superbases. 2. Preparation of 1,3-Unsubstituted and 1-Substituted 2-Iminoimidazolidine Derivatives and a Related Guanidine by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas

  摘要：

  Simple preparation methods for modified guanidines were explored for new chiral superbases, Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S)-1,2-diphenylethylenediamine and (1R,2R)- or (1S,2S)-1,2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,SS)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.

  DOI：

  10.1021/jo000745n

文献信息

• Enantio- and Diastereoselective Variations on α-Iminonitriles: Harnessing Chiral Cyclopropenimine-Thiourea Organocatalysts
  作者：Hooseung Lee、Hyeongwoo Nam、Sarah Yunmi Lee

  DOI：10.1021/jacs.3c09911

  日期：2024.2.7

  Chiral 1-pyrrolines containing a nitrile motif serve as crucial structural scaffolds in biologically active molecules and exhibit diversity as building blocks owing to their valuable functional groups; however, the asymmetric synthesis of such compounds remains largely unexplored. Herein, we present an enantio- and diastereoselective method for the synthesis of α-chiral nitrile-containing 1-pyrroline

  含有腈基序的手性 1-吡咯啉可作为生物活性分子中重要的结构支架，并由于其有价值的官能团而表现出作为构建块的多样性；然而，此类化合物的不对称合成在很大程度上仍未得到探索。在此，我们提出了一种对映和非对映选择性方法，通过设计和引入具有硫脲部分的手性环丙烯亚胺基双功能催化剂，合成带有邻位立构中心的α-手性含腈1-吡咯啉衍生物。该合成需要将 α-亚氨基腈与多种烯酮进行高度立体选择性的共轭加成，然后进行环缩合，从而得到一系列氰基吡咯啉衍生物，其中一些含有全碳四元中心。此外，我们通过在 1% 催化剂负载下进行克级反应以及产品的各种化学选择性转化（包括维格列汀类似物的合成）来证明该策略的合成效用。最后，我们展示了通过反式异构化选择性合成氰基吡咯啉产品的所有四种立体异构体，突出了我们方法的多功能性。
• Modified Guanidines as Potential Chiral Superbases. 2. Preparation of 1,3-Unsubstituted and 1-Substituted 2-Iminoimidazolidine Derivatives and a Related Guanidine by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas
  作者：Toshio Isobe、Keiko Fukuda、Tatsuhiro Tokunaga、Hiroko Seki、Kentaro Yamaguchi、Tsutomu Ishikawa

  DOI：10.1021/jo000745n

  日期：2000.11.1

  Simple preparation methods for modified guanidines were explored for new chiral superbases, Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S)-1,2-diphenylethylenediamine and (1R,2R)- or (1S,2S)-1,2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,SS)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.